Trifluoroacetic acid → HCID 86712428, compound

HRID 469034Notes

Reaction equation

HRID 469034 reaction equation
[C:1](O)([C:3]([F:6])([F:5])[F:4])=[O:2].[NH:8]1[CH2:12][CH2:11][N:10]=[C:9]1[C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][NH2:21])=[CH:15][CH:14]=1.[CH3:22][O:23][C:24]1[CH:29]=[C:28]([CH3:30])[C:27]([S:31]([N:34]([CH3:45])[CH:35]([C:37]2[O:41][CH:40]=[C:39]([C:42](O)=[O:43])[CH:38]=2)[CH3:36])(=[O:33])=[O:32])=[C:26]([CH3:46])[CH:25]=1.CCN=C=NCCCN(C)C.C1C=C2N=NN(O)C2=CC=1.O>CN(C=O)C>[F:4][C:3]([F:6])([F:5])[C:1]([NH2:8])=[O:2].[NH:10]1[CH2:11][CH2:12][N:8]=[C:9]1[C:13]1[CH:14]=[CH:15][C:16]([CH2:19][CH2:20][NH:21][C:42]([C:39]2[CH:38]=[C:37]([CH:35]([N:34]([S:31]([C:27]3[C:26]([CH3:46])=[CH:25][C:24]([O:23][CH3:22])=[CH:29][C:28]=3[CH3:30])(=[O:33])=[O:32])[CH3:45])[CH3:36])[O:41][CH:40]=2)=[O:43])=[CH:17][CH:18]=1

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 223907052-[4-(4,5-Dihydro-1H-imidazol-2-yl)phenyl]ethan-1-amineHCID 58393040HCID 58393040, compound

Product 1

HCID 86712428HCID 86712428, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared according to general procedure AH using the bis TFA salt of 2-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]ethanamine, (40 mg, 0.1 mmol), TEA (0.05 mL, 0.32 mmol), DMF (1 mL), 5-(1-{[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}ethyl)furan-3-carboxylic acid (39 mg, 0.11 mmol), EDCI (24 mg, 0.13 mmol) and HOBt monohydrate (17 mg, 0.13 mmol). The crude product was purified using MP-TsOH resin, washing with MeOH (5 mL) and eluting with 7N NH3 in MeOH (7 mL). A portion of the resulting partially purified product was purified using prep method C to afford the title compound.

Workup

  1. customThe title compound was prepared
  2. customThe crude product was purified
  3. washwashing with MeOH (5 mL)
  4. washeluting with 7N NH3 in MeOH (7 mL)
  5. customA portion of the resulting partially purified product was purified

Sources & evidence

ORD record
ord-e2bd8799acfa4afebb10c900752ce5eb
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

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